Synthesis of C-5-substituted resorcylates and resorcinamides via formylation-aromatization of functionalized keto-dioxinones

被引：4

作者：

Barrett, Tim N. ^{[1
]}

Patel, Bhavesh H. ^{[1
]}

Barrett, Anthony G. M. ^{[1
]}

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AY, England

来源：

TETRAHEDRON | 2014年 / 70卷 / 38期

基金：

英国工程与自然科学研究理事会; 欧洲研究理事会;

关键词：

Resorcylates; Resorcinamides; Keto-dioxinones; Aromatization; CHAPERONE HSP90; INHIBITOR; DISCOVERY;

D O I：

10.1016/j.tet.2014.06.099

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Efficient syntheses of diverse substituted resorcylates and resorcinamides from keto-dioxinones are described. Functionalized 6-keto-2,2-dimethyl-4H-1,3-dioxin-4-ones, generated via enolate acylation or alkylation reactions, were subsequently C-formylated and cyclized to the corresponding arenes. Further manipulations gave a wide range of structures of potential pharmaceutical interest including C-5-substituted, C-4,5-cyclo-fused and C-5,6-cyclo-fused resorcylates, as well as resorcinamides related to the Hsp90 inhibitor AT13387. The syntheses are noted for brevity with a maximum of 5 synthetic steps and without the need for protection of phenol groups. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：6894 / 6901

页数：8

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